Design, synthesis and HIV-RT inhibitory activity of novel thiazolidin-4-one derivatives

2011, Volume 5, Issue 2

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Frontiers of Chemical Science and Engineering >> 2011, Volume 5, Issue 2 doi: 10.1007/s11705-010-1022-7

Design, synthesis and HIV-RT inhibitory activity of novel thiazolidin-4-one derivatives

Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China

Available online: 2011-06-05

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Abstract

A series of 2-aryl-3-(4,5,6-trimethylpyrimidin-2-yl) thiazolidin-4-ones ( – ) and their derivatives bearing a lipophilic substituent, like acetoxy group ( – ), propionyloxy group ( – ), methyl ( and ) at C-5 on thiazolidin-4-one ring were designed, synthesized and evaluated for their HIV-RT inhibitory activity. Using self-catalyzed Pummerer reaction, compounds – and – were obtained in good yield (63.1% 75.2%). Preliminary anti-HIV-RT test of these derivatives indicated that compounds – , (propionyloxy group at C-5) showed moderate HIV-RT inhibitory activity and compounds and with methyl at C-5 showed a weak HIV-RT inhibitory activity. Structure activity relationship analysis suggested that the substituted groups on C-5 would be unfavorable to anti-HIV-RT activity and that the steric effect might play a critical role in the anti-HIV RT activity.

Keywords

5-subsituted thiazolidin-4-ones ; Pummerer reaction ; anti-HIV-RT activity ; SARs

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